From Self-Employed To Salaried: Success Stories

When I tell career coaching clients that self-employed freelancing or consulting can be good paths toward landing full-time salaried employment, many people express skepticism that this strategy ever works. Perhaps because many recruiters are unenthusiastic about self-employed job seekers, there is a persistent myth in the workplace that once you are a freelancer or consultant, you will never again be employable by organizations. I am a huge fan of self-employment, but I am also a realist who understands that there are circumstances under which many people would be happy accepting a salaried job, so it is helpful for them to know that making connections via freelance or consulting work is actually a great way to land salaried work.

Freelance vs. Salaried

To prove that you can be hired into a full-time salaried position after working as a freelancer or consultant, I found six people who transitioned from a W-9 role to a W-2 role and I asked them to respond to these questions:

– What type of freelancing or consulting were you doing when you were hired into a salaried role?

– How was the transition?

– What advice do you have for consultants or freelancers who are considering a similar career move?

Here are their responses:

David Bakke, Editor, Money Crashers

Salaried Employment “I did some freelance writing and marketing work for a client and it eventually turned into a full-time writing and marketing position. The transition was fairly smooth overall, but there are several things to be aware of for someone considering making that move. The positives are you go from an inconsistent income to a steady paycheck. You may pay less for health insurance (and have better benefits) as well. You get to be around co-workers and supervisors as well. You may also enjoy a bit more job security. If you had clients in the past that didn’t pay you in a timely fashion, you won’t have to deal with that anymore either. You also get paid holidays and paid time off.

On the other hand, you won’t get to work the hours you choose anymore, dealing directly with a supervisor can be challenging, and then there’s also having to get up at a certain time each morning and dealing with traffic.

A final consideration is that you also miss out on certain tax deductions.”

Maggie Young, Communications Specialist, B&B

“I started my career as a freelancer, picked up by a prominent print company to help with content creation and copywriting. I knew nothing of the print industry and really had to dive deep to understand enough to write intelligently. I was working under a new Marketing Director who focused on a complete brand overhaul. The rebranding process became so involved that my workload grew, and I started taking on projects that I’ve never worked on before. I was learning about marketing as I was freelancing.

Shortly after the rebranding, the Marketing Director left, which left a hole for me to fill. The president offered me a full time job and I soon became the Marketing Specialist. I am the one and only person in the marketing department, which has given me a lot of room to test different initiatives and daily increase my knowledge of both the print and marketing industry.

I think the biggest thing for freelancers to consider is that their schedules will become much more restricted when they move to a full-time position. No more taking a break at 2 pm and picking it back up at 5. My job is 9-5, no ifs, ands, or buts about it!

While I miss the schedule I once had, I don’t miss the insecurity I felt by not having a full-time position. I also spent a lot of time alone for various projects, but now that I’m fully engaged in the office environment, it’s easier for me to bounce ideas off of my colleagues and feel the workplace camaraderie I was missing out on as a consultant.”

Jessica Greenwalt, Graphic Designer, CrowdMed and Pixelkeet

“I was a freelance graphic designer, illustrator, and web developer for over ten years. I’ve produced projects for hundreds of clients from all over the world, including LinkedIn, UC Berkeley, Marvel Comics, Telefónica, and many more. I loved being a freelancer — picking my projects, traveling the world and working on my own schedule — but in April of 2013, I was convinced to join one of my client’s companies, CrowdMed, full time.

I ultimately decided to join because the company is a San Francisco startup that is doing something amazing, using the wisdom of crowds to solve medical mysteries, and the CEO made me an awesome deal in which I still get to spend about 20% of my time working on my freelance graphic design business.

At CrowdMed, we are changing the way medical diagnosis is done to help patients arrive at an answer faster than ever before, saving them from prolonged suffering and spending thousands on misdirected tests and procedures. When I was in college, I had been through a painful diagnosis process (I’ve been poked, scanned, and biopsied multiple times before doctors could come to a conclusion) at a great cost to myself, both in time and money (two things that are scarce when you are in college). I was furious about the process, but at the time, I had no idea what could be done to change it. I had accepted this mess of meetings and procedures as how the medical system operated.

But at the end of 2012, CrowdMed’s CEO told me about how their website will allow patients to get a list of suggested diagnoses from a “crowd” online (composed of both medical experts and laypeople) at a fraction of the time and cost it would take them to get the same diagnoses from a doctor. I told him he was crazy, but my design firm, Pixelkeet, started working on CrowdMed’s website and marketing materials. When the site was ready, I submitted my case to CrowdMed to see how the crowd’s answers would compare to my doctors’. The crowd was able to accurately diagnose me without the barrage of medical tests and visits, just by reading the symptoms I had typed into my case. After that, when the CEO asked me again to join CrowdMed full time, I agreed because I want to be a part of something that can save other patients from going through what I went through, or worse.

I made the right choice. I’ve been having a great time working in-house for CrowdMed and working on interesting projects on the side. Of course, Pixelkeet is still my baby. Even when I started my own design firm, I lived like the freelancer I had been for years previously. Taking only the projects I wanted to, sleeping in, working in my pjs, traveling where I wanted, when I wanted without having to request time off from a boss. I love the freelance lifestyle. As a freelancer and owner of a design firm, I woke up every day happy and satisfied with my life.

Now, I love that I can use my skills as a designer and web developer to help people and to disrupt a system so desperately in need of change. Working at CrowdMed gives me a different kind of satisfaction–the satisfaction that comes along with working on something that may have a greater impact on the lives of others than I had ever hoped to achieve as a freelancer.

I’ve also discovered that I really enjoy working with my team on building this startup. We’re a small group — only three people — and we get along and work together really well. My team has become like family to me. Had I stuck to freelancing, I would have missed out on being a part of a team like this. I wouldn’t have known just how rewarding working in a company can be, when you’re working with the right people.”

Brian Massie, Chief Communication Officer, Bogan’s Distillery

“I’ve been a communication consultant for more than six years and I just accepted a CCO position with a former client. When I say communication consulting, I mean my firm is one stop shopping for communication needs including: advertising, public relations, social media, events, lobbying, brand development, and more. My new employer was one of my best paying clients and when he sold his interest in a small business and decided to start a larger one, he wanted me running the communication program.

I’m operating my practice until the end of the year after which I’ll move from VA to MD to take the new job. The compensation package provides a 40% increase relative to my current package. As CCO I also have complete control so I don’t have to ask permission or wait for approval; things just get done.

In my opinion, this is the *best* way to get a job. During every aspect of the professional relationship, neither party was/is in a position of weakness. When he was a client, neither one of us needed the other financially but both sides benefited from the relationship. When the discussion was had about the new business I was negotiating from the position of already having a rewarding occupation. As a result, I was able to spell out what compensation I wanted and he didn’t argue because he knows I’m worth it.

I would advise anyone looking to make a similar move to evaluate what that person/organization was like to work with and compare the power you held with them as a client to the power you’ll have with them as an employer. An increase in power and compensation are promising signs that they really want you. If you’re merely jumping ship from your current to have the same power and compensation, you might be better off where you are.”

Art Therapy

Andrea Cooper, Artist-Facilitator, Therapeutic Art Program, Mercy Medical Center

“I was a freelance graphic designer and one of my clients was the Attorney General of Maryland. I worked on a quarterly publication for them. After about a year, they offered to create a position for me to work on all of their publications for consumers, reports and displays. It was a good transition for me because, as a freelancer, although I made more hourly, I had no benefits and my income was fluctuating in nature. So, although my hourly rate was less, I gained health insurance for my family, vacation and sick leave as well as a predictable income. As the mother of two young children with a self-employed husband, this was extremely important. I stayed there for 15 years and left only to pursue a different line of work that suited my lifestyle better as I got a bit older.”

Graeme Gibson, Strategist, Dental Departures

“I’ve had a relatively unexpected career shift, and am still surprised the way it all happened. For a number of years I have worked on internet related marketing for a non-profit, as well as negotiating travel costs for the entire group.  A parent involved in the group noticed how tenacious I was and passed my name onto a local startup who needed help in all of these areas.

Since the company was bootstrapping it, they also needed a reliable person at an affordable cost.  All of this fit me to a tee.

I was advising on their internet marketing strategy, social media strategy, and advised on strategic relationships that would help the company and our customers. When I was finally hired as an employee my role still involved those things, but I was put in charge of delegating and managing a small group of people to complete tasks I would come up with and assign to them.

It was easy to convince me to make this career move. I enjoyed working with the main executive group I started with, and we were able to have an honest rapport that is rare in most companies. While they did offer a raise in salary and generous stock incentive, it was the actions of the development lead, customer service manager, and the vision of the CEO, Paul McTaggart, that made me want to stick around beyond the role of a consultant.

While I feel the transition has been seamless, I feel a much greater deal of pressure since my performance is based on how my entire team functions. There is a greater expectation of setting and reaching goals, but so far so good. My role as an employee does not allow me the luxury of saying my piece and moving on with my next project or adventure. I feel far more vested on a professional and person level now that Dental Departures has hired me full time.

My best advice is to consider how you get along with and relate to the executive team and managers to whom you will be reporting. I believe one of the biggest mistakes you can make is getting involved with a company that does not share the same vision, ethics, and goals that hold true for you. However, if the future of the company looks promising and you enjoy your time with your co-workers, go for it. It certainly has worked out for me.”

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